Asymmetric synthesis of (+)-(3aS,4S,7aS)-3a-hydroxy-4,7a- dimethylperhydroindane-1,5-dione

Tetrahedron Asymmetry

Volumn 8, Issue 13, 1997, Pages 2075-2077

  Medarde, Manuel ^a   Caballero, Esther ^a   Melero, Concepción P ^a   Tomé, Fernando ^a   San Feliciano, Arturo ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARDENOLIDE DERIVATIVE; INDAN DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030796607     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00209-7     Document Type: Article

References (18)

1. Z.G. Hajos and D.R. Parrish J. Org. Chem. 1974, 39, 1612-1615; 1615-1621.
2. M. Medarde; E. Caballero; F. Tomé; P.G. Gracia; M. Boya and A. San Feliciano Synt. Commun. 1995, 25, 1377-1382.
3. M. Medarde; F. Tomé; J.L. López; E. Caballero; M. Boya; C.P. Melero and A. San Feliciano Tetrahedron Lett. 1994, 35, 8683-8686.
4. M. Medarde; E. Caballero; F. Tomé; C.P. Melero; M. Boya and A. San Feliciano An. Quim. 1995, 91, 89-94.
5. Z.G. Hajos and D.R. Parrish 1976 US.Pat. 3,975,440 and 3,975,442.
6. S. Danishesfky and P. Cain J. Am. Chem. Soc. 1976,98,4975-4982. P. Buchschacher; J.-M. Cassal; A. Fürst and W. Meier Helv. Chim. Acta 1977, 60, 2747-2755. U. Eder; G. Sauer and R. Wiechert Angew. Chem. 1971, 83, 492-493. J. Martens and S. Lübben Arch. Pharm. 1991, 324, 59-60.
7. S. Danishesfky and P. Cain J. Am. Chem. Soc. 1976,98,4975-4982. P. Buchschacher; J.-M. Cassal; A. Fürst and W. Meier Helv. Chim. Acta 1977, 60, 2747-2755. U. Eder; G. Sauer and R. Wiechert Angew. Chem. 1971, 83, 492-493. J. Martens and S. Lübben Arch. Pharm. 1991, 324, 59-60.
8. S. Danishesfky and P. Cain J. Am. Chem. Soc. 1976,98,4975-4982. P. Buchschacher; J.-M. Cassal; A. Fürst and W. Meier Helv. Chim. Acta 1977, 60, 2747-2755. U. Eder; G. Sauer and R. Wiechert Angew. Chem. 1971, 83, 492-493. J. Martens and S. Lübben Arch. Pharm. 1991, 324, 59-60.
9. S. Danishesfky and P. Cain J. Am. Chem. Soc. 1976,98,4975-4982. P. Buchschacher; J.-M. Cassal; A. Fürst and W. Meier Helv. Chim. Acta 1977, 60, 2747-2755. U. Eder; G. Sauer and R. Wiechert Angew. Chem. 1971, 83, 492-493. J. Martens and S. Lübben Arch. Pharm. 1991, 324, 59-60.
10. Z.G. Hajos and D.R. Parrish Org. Synth. 1984, 63, 26-30.
11. I. Shimizu; Y. Naito and J. Tsuji Tetrahedron Lett. 1980, 21, 487-490. R.A. Micheli; Z.G. Hajos; N. Cohen; D.R. Parrish; L.A. Portland; W. Sciamanna; M.A. Scott and P.A. Wehrli J. Org. Chem. 1975, 40, 675-681. G. Sauer; U. Eder; G. Haffer; G. Neef and R. Wiechert Angew. Chem. Int. Ed. 1975, 14, 417.
12. I. Shimizu; Y. Naito and J. Tsuji Tetrahedron Lett. 1980, 21, 487-490. R.A. Micheli; Z.G. Hajos; N. Cohen; D.R. Parrish; L.A. Portland; W. Sciamanna; M.A. Scott and P.A. Wehrli J. Org. Chem. 1975, 40, 675-681. G. Sauer; U. Eder; G. Haffer; G. Neef and R. Wiechert Angew. Chem. Int. Ed. 1975, 14, 417.
13. I. Shimizu; Y. Naito and J. Tsuji Tetrahedron Lett. 1980, 21, 487-490. R.A. Micheli; Z.G. Hajos; N. Cohen; D.R. Parrish; L.A. Portland; W. Sciamanna; M.A. Scott and P.A. Wehrli J. Org. Chem. 1975, 40, 675-681. G. Sauer; U. Eder; G. Haffer; G. Neef and R. Wiechert Angew. Chem. Int. Ed. 1975, 14, 417.
14. D. Rajagopal; K. Rajagopalan and S. Swaminathan Tetrahedron Asymmetry 1996, 7, 2189-2190.
15. C. Agami; C. Puchot and H. Sevestre Tetrahedron Lett. 1986, 27, 1501-1504. C. Agami; F. Meynier; C. Puchot; J. Guilhem and C. Pascard Tetrahedron 1984, 40, 1031-1038. C. Agami Bull. Soc. Chim. Fr. 1988, 499-507.
16. C. Agami; C. Puchot and H. Sevestre Tetrahedron Lett. 1986, 27, 1501-1504. C. Agami; F. Meynier; C. Puchot; J. Guilhem and C. Pascard Tetrahedron 1984, 40, 1031-1038. C. Agami Bull. Soc. Chim. Fr. 1988, 499-507.
17. C. Agami; C. Puchot and H. Sevestre Tetrahedron Lett. 1986, 27, 1501-1504. C. Agami; F. Meynier; C. Puchot; J. Guilhem and C. Pascard Tetrahedron 1984, 40, 1031-1038. C. Agami Bull. Soc. Chim. Fr. 1988, 499-507.
18. 3): 219.2(1), 28.3(2), 36.4(3), 84.5(3a), 50.9(4), 209.6(5), 29.8(6), 32.7(7), 53.6(7a), 12.5(8), 6.7(9). Relative stereochemistry at C-4 established by the nOe observed at H-4 upon irradiation of Me-8.